An awesome place I've visited:

Maui! I went in winter, it transported me back to summer. it was great getting off the beach and seeing Christmas trees. We went to a different beach everyday, explored the town at night.

The movie I've watched the most times:

It has to be Dumb and Dumber. I know it inside and out, yet it feels like the first time every time. Gladiator is a close second.